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ethyl (1R,3R,4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate → HCID 10535139, compound

HRID 347803
Notes
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Reaction equation

HRID 347803 reaction equation
C1([C@@H]([N:9]2[C@@H:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C@H:13]3[CH2:20][C@@H:10]2[CH:11]=[CH:12]3)C)C=CC=CC=1>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C@@H:10]12[CH2:20][C@@H:13]([CH2:12][CH2:11]1)[C@H:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:9]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 10730826ethyl (1R,3R,4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Product 1

HCID 10535139HCID 10535139, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl (1R, 3R, 4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (3.84 g, 14.2 mmol) in ethyl acetate (28 ml) was added 20 wt % Pd(OH)2 (4.97 g), and the mixture was stirred under a hydrogen atmosphere at 45° C. 64 hours. After a filtration through Celite, the solvent was concentrated. The residue was purified by silica gel column chromatography (1%–5% methanol/chloroform), to give ethyl (1S, 3R, 4R)-2-azabicyclo[2.2.1]heptane-3-carboxylate (0.595 g, 25%).

Workup

  1. custom64 hours
  2. filtrationAfter a filtration through Celite
  3. concentrationthe solvent was concentrated
  4. customThe residue was purified by silica gel column chromatography (1%–5% methanol/chloroform)

Sources & evidence

ORD record
ord-d7b5cdf74ea5440e82f03564ec2c1922
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176217B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes